کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346940 980286 2009 4 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita–Baylis–Hillman reactions of acrylates with aromatic aldehydes
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
پیش نمایش صفحه اول مقاله
Valine-derived phosphinothiourea as organocatalyst in enantioselective Morita–Baylis–Hillman reactions of acrylates with aromatic aldehydes
چکیده انگلیسی

A new type of chiral bifunctional phosphinothiourea derived from l-valine is synthesized and used as an organocatalyst in the enantioselective Morita–Baylis–Hillman reaction of aromatic aldehydes with acrylates. The desired products were obtained in good enantioselectivities (up to 83% ee) and in excellent yields (up to 96%) under mild reaction conditions.

Figure optionsDownload as PowerPoint slide

(S)-1-(1-Diphenylphosphino3-methylbutan-2-yl)-3-phenylthioureaC24H27N2PS[α]D25=+32.1 (c 0.7, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-Diphenylphosphino-3-methylbutan-2-yl)-3-(4-methoxyphenyl)thioureaC25H29N2OPS[α]D25=+51.0 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(4-Chlorophenyl)-3-(1-diphenylphosphino-3-methylbutan-2-yl)thioureaC24H26ClN2PS[α]D25=+59.0 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(3,5-Bis(trifluoromethyl)phenyl)-3-(1-diphenylphosphino-3-methylbutan-2-yl)thioureaC26H25N2F6PS[α]D25=+7.0 (c 0.5, CH2Cl2)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-Cyclohexyl-3-(1-diphenylphosphino-3-methylbutan-2-yl)thioureaC24H33N2PS[α]D25=-81.7 (c 0.3, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

(S)-1-(1-Diphenylphosphino-3-methylbutan-2-yl)-3-octylthioureaC26H39N2PS[α]D25=-11.0 (c 0.5, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 20, Issue 18, 23 September 2009, Pages 2117–2120
نویسندگان
, , ,